Characteristics and antioxidant activity of Maillard reaction products from fructose-glycine oligomer

Food Science and Biotechnology

Volumn 19, Issue 4, 2010, Pages 929-940

  Kim, Ji Sang ^a   Lee, Young Soon ^a  

^a Kyung Hee University   (South Korea)

Author keywords

Antioxidant activity; Characteristics; Glycine oligomer; Maillard reaction product (MRP)

Indexed keywords

ABSORBANCES; ANTIOXIDANT ACTIVITIES; CHARACTERISTICS; CHELATING ACTIVITY; ENOLIZATION; FERRIC REDUCING ABILITY OF PLASMAS; GEL PERMEATION CHROMATOGRAMS; GLYCINE OLIGOMER; HEATING TIME; MAILLARD REACTION PRODUCTS; MODEL SYSTEM; RADICAL SCAVENGING ACTIVITY; RETENTION TIME;

AMINO ACIDS; ASSAYS; CHROMATOGRAPHIC ANALYSIS; FRUCTOSE; GLYCOSYLATION; HEATING; REACTION PRODUCTS;

OLIGOMERS;

EID: 79957640089     PISSN: 12267708     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10068-010-0131-x     Document Type: Article

References (53)

1. Hodge JE. Chemistry of browning reactions in model systems. J. Agr. Food Chem. 1: 928-934 (1953)
2. Wijewickreme AN, Kitts DD, Durance TD. Reaction conditions influence the elementary composition and metal chelating affinity of nondialyzable model Maillard reaction products. J. Agr. Food Chem. 45: 4577-4583 (1997)
3. Eichner K. Antioxidant effect of Maillard reaction intermediates. Prog. Food. Nutr. Sci. 5: 441-451 (1981)
4. Morales FJ, Jimenez-Perez S. Free radical scavenging capacity of Maillard reaction products as related to color and fluorescence. Food Chem. 72: 119-125 (2001)
5. Bersuder P, Hole M, Smith G. Antioxidants from a heated histidineglucose model system. Investigation of the copper (II) binding ability. J. Am. Oil Chem. Soc. 78: 1079-1082 (2001)
6. Bevers HAJM, Wijntje R, De Haan AB. Analysis of fructose, glycine, and triglycine using HPLC UV-vis detection and evaporative light-scattering detection. Spectroscopy 21: 52-61 (2006)
7. Hartman R, Meisel H. Food-derived peptides with biological activity: From research to food applications. Curr. Opin. Biotech. 18: 163-169 (2007)
8. Lu CY, Hao Z, Payne R, Ho CT. Effects of water content on volatile generation and peptide degradation in the Maillard reaction of glycine, diglycine, and triglycine. J. Agr. Food Chem. 53: 6443-6447 (2005)
9. Oh YC, Shu CK, Ho CT. Some volatiles compounds formed from thermal interaction of glucose with glycine, diglycine, triglycine, and tetraglycine. J. Agr. Food Chem. 39: 1553-1554 (1991)
10. th ed. Merck & Co., Whitehouse Station, NJ, USA. pp. 1477-1478 (1996)
11. Ajandouz EH, Tchiakpe LS, Ore FD, Benajiba A, Puigserver A. Effects of pH on caramelization and Maillard reaction kinetics in fructose-lysine model systems. J. Food Sci. 66: 926-931 (2001)
12. Wang L, Xiong YL. Inhibition of lipid oxidation in cooked beef patties by hydrolyzed potato protein is related to its reducing and radical scavenging ability. J. Agr. Food Chem. 53: 9186-9192 (2005)
13. Dinis TCP, Madeira VMC, Almerida LM. Action of phenolic derivatives (acetoaminophen, salycilate, and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavenges. Arch. Biochem. Biophys. 315: 161-169 (1994)
14. Yen GC, Hsieh PP. Antioxidative activity and scavenging effects on xylose-lysine Maillard reaction products. J. Sci. Food Agr. 67: 415-420 (1995)
15. Benzie IFF, Strain JJ. The ferric reducing ability of plasma (FRAP) as a measure of antioxidant power the FRAP assay. Anal. Biochem. 239: 70-76 (1996)
16. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Bio. Med. 26: 1231-1237 (1999)
17. Benjakul S, Lertittikul W, Bauer F. Antioxidant activity of Maillard reaction products from a porcine plasma protein-sugar model system. Food Chem. 93: 189-196 (2005)
18. Kim JS, Lee YS. Antioxidant activity of Maillard reaction products derived from aqueous glucose/glycine, diglycine, and triglycine model systems as a function of heating time. Food Chem. 116: 227-232 (2009)
19. Kim JS, Lee YS. Study of Maillard reaction products derived from aqueous model systems with different peptide chain lengths. Food Chem. 116: 846-853 (2009)
20. Ogura K, Nakayama M, Nakaoka K, Nishihata Y. Spectroelectrochemical and EQCM studies on the oxidation of glycilpeptides in alkaline medium. J. Electroanal. Chem. 482: 32-39 (2000)
21. Huber C, Wachtershauser G. Peptides by activation of amino acids with CO on (Ni, Fe)S surfaces: Implications for the origin of life. Science 281: 670-671 (1998)
22. Chuyen NV, Kurata T, Fujimaki M. Studies on the reaction of dipeptides with glyoxal. Agr. Biol. Chem. Tokyo 37: 327-334 (1973)
23. Reynols TM. Non-enzymatic browning. Sugar-amine interaction. p. 219In: Carbohydrates and Their Roles. Shultz HW (ed). AVI Pub. Co., Westport, CT, USA (1969)
24. Buera MDP, Chirife J, Resnik SL, Lozano RD. Nonenzymatic browning in liquid model systems of high water activity: Kinetics of color changes due to reaction between glucose and glycine peptides. J. Food Sci. 52: 1059-1062 (1987)
25. Maillard LC, Gautier MA. The reaction of amino acids with sugars: Mechanisms of melanoid formation. C. R. Seances Acad. Sci. III 154: 66-68 (1912)
26. Reynolds TM. Chemistry of nonenzymic browning II. Adv. Food Res. 14: 167-283 (1965)
27. Mauron J. The Maillard reaction in food: A critical review from the nutritional standpoint. Prog. Food. Nutr. Sci. 5: 5-35 (1981)
28. Shin DB, Hayase F, Kato H. Polymerization of proteins caused by reaction with sugars and the formation of 3-deoxyglucosone under physiological conditions. Agr. Biol. Chem. Tokyo 52: 1451-1458 (1988)
29. Burton HS, McWeeny DJ, Biltcliffe DO. Sulphur dioxide and ketose-amino reactions. Chem. Indust. 27: 693-695 (1963)
30. Reynolds TM. Chemistry of nonenzymic browning. III. Effect of bisulphite, phosphate, and malate on the reaction of glycine and glucose. Aust. J. Chem. 12: 265-274 (1959)
31. Suárez G, Maturana J, Oronsky AL, Raventós-Suárez C. Fructose induced fluoresence generation of reductively methylated glycated bovine serum albumin: Evidence for nonenzymatic glycation of Amadori adducts. Biochim. Biophys. Acta 1075: 12-19 (1991)
32. Ivanov CP, Ivanov OC, Simeonova RA, Mirkova GD. A study of the interaction of glycine and its oligohomopeptides with formaldehyde and acetaldehyde under possible primitive earth conditions. Origins Life Evol. B 13: 97-108 (1983)
33. Brands CMJ, Van Boekel MAJS. Reactions of monosaccharides during heating of sugar-casein systems: Building of a reaction network model. J. Agr. Food Chem. 49: 4667-4675 (2001)
34. De Kok PMT, Rosing EAE. Reactivity of peptides in Maillard reaction. pp. 158-179. In: Thermally Generated Flavors: Maillard, Microwave, and Extrusion Processes. Parliment TH, Morello MJ, McGomn RJ (eds). American Chemical Society, Washington, DC, USA (1994)
35. Van Boekel MAJS. Kinetic modelling of sugar reactions in heated milk-like systems. Neth. Milk Dairy J. 50: 245-266 (1996)
36. Kim JS, Lee YS. Effect of reaction pH on enolization and racemization reactions of glucose and fructose on heating with amino acid enantiomers and formation of melanoidins as result of the Maillard reaction. Food Chem. 108: 582-592 (2008)
37. Nagayama M, Takaoka O, Inomata K, Yamagata Y. Diketopiperazine-mediated peptide formation in aqueous solution. Origins Life Evol. B 20: 249-257 (1990)
38. Imai E, Honda H, Hatori K, Brack A, Matsuno K. Elongation of oligopeptides in a simulated submarine hydrothermal system. Science 283: 831-833 (1990)
39. Hofmann T. Studies on the relationship between Mw and the color potency of fractions obtained by thermal treatment of glucose/amino acid and glucose/protein solutions by using ultracentrifugation and color dilution techniques. J. Agr. Food Chem. 46: 3891-3895 (1998)
40. Delgado-Andrade C, Seiquer I, Navarro P. Bioavailability of iron from a heat treated glucose-lysine model food system: Assays in rats and in Caco-2 cells. J. Sci. Food Agr. 84: 1507-1513 (2004)
41. Jing H, Kitts DD. Antioxidant activity of sugar-lysine Maillard reaction products in cell free and cell culture systems. Arch. Biochem. Biophys. 429: 154-163 (2004)
42. Yoshimura Y, Ujima T, Watanabe T, Nakazawa H. Antioxidative effect of Maillard reaction products using glucose-glycine model system. J. Agr. Food Chem. 45: 4106-4109 (1997)
43. Morales FJ, Fernandez-Fraguas C, Jiménez-Pérez S. Iron binding ability of melanoidins from food and model systems. Food Chem. 90: 821-827 (2005)
44. O'Brien JO, Morrissey PA. Metal ion complexation by products of the Maillard reaction. Food Chem. 58: 17-27 (1997)
45. Seifert ST, Krause RM, Gloe K, Henle T. Metal complexation by the peptide-bound maillard reaction products N(ε)-fructoselysine and N(ε)-carboxymethyllysine. J. Agr. Food Chem. 52: 2347-2350 (2004)
46. Wijewickreme AN, Kitts DD. Metal chelating and antioxidant activity of model Maillard reaction products. Adv. Exp. Med. Biol. 36: 543-553 (1998)
47. Shon MY, Kim TH, Sung NJ. Antioxidants and free radical scavenging activity of Phellinus baumii extracts. Food Chem. 82: 593-597 (2003)
48. Shih PW, Lai PL, Jen HWK. Antioxidant activities of aqueous extracts of selected plants. Food Chem. 99: 775-783 (2006)
49. Chen HM, Muramoto K, Yamauchi F, Fujimoto K, Nokihara K. Antioxidant properties of histidine-containing peptides designed from peptide fragment found in the digests of a soybean protein. J. Agr. Food Chem. 46: 49-53 (1998)
50. Zhou S, Decker EA. Ability of amino acids, dipeptides, polyamines, and sulfhydryls to quench hexanal, a saturated aldehydic lipid oxidation product. J. Agr. Food Chem. 47: 1932-1936 (1999)
51. Yamaguchi N, Yokoo Y, Fujimaki M. Studies on antioxidative activities of amino compounds on fats and oils. Part II. Antioxidative activities of dipeptides and their synergistic effects on tocopherol. Nippon Shokuhin Kogyo Gakk. 22: 425-430 (1975)
52. Wu HC, Chen HM, Shiau CY. Free amino acids and peptides as related to antioxidant properties in protein hydrolysates of mackerel (Scomber austriasicus). Food Res. Int. 36: 949-957 (2003)
53. Rufián-Henares JA, Morales FJ. Functional properties of melanoidins: In vitro antioxidant, antimicrobial, and antihypertensive activities. Food Res. Int. 40: 995-1002 (2007)